tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane
• CAS No.: 889109-12-0
• Molecular Formula: C₂₉H₄₆O₄SSi
• Molecular Weight: 518.833

Synonyms:tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

There total 12 articles about tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(R)-3-[(2S,3R,4aS,8aS,9aR,10aR)-3-(tert-Butyl-dimethyl-silanyloxy)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-2-yl]-2-methyl-propan-1-ol (889109-11-9) + diphenyldisulfane (882-33-7) → tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane (889109-12-0)

Guidance literature:

With tributylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/jo0603025

Reference yield:

(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene (858346-53-9) → tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane (889109-12-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂ / Pd(OH)2/C / ethyl acetate / 4 h

2.1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C

3.1: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: tetrahydrofuran / 0.5 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: NaHMDS / tetrahydrofuran / 0 °C

7.2: 298 mg / tetrahydrofuran / 1 h / 20 °C

8.1: 84 percent / DDQ; aq. NaHCO₃ / CH₂Cl₂ / 1.5 h / 45 °C

9.1: KH / tetrahydrofuran / 1 h / 0 °C

10.1: 176 mg / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 20 h / 20 °C

11.1: 95 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

12.1: 95 percent / Bu₃P / dimethylformamide / 4 h / 20 °C

With Grubbs catalyst first generation; oxalyl dichloride; trimethylsilyl iodide; tributylphosphine; camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; potassium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.1: Grignard reaction / 6.1: Swern oxidation / 7.2: Wittig reaction;

DOI:10.1021/jo0603025

Reference yield:

(2R,3S,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-hydroxymethyl-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol → tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane (889109-12-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C

2.1: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: tetrahydrofuran / 0.5 h / 0 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: NaHMDS / tetrahydrofuran / 0 °C

6.2: 298 mg / tetrahydrofuran / 1 h / 20 °C

7.1: 84 percent / DDQ; aq. NaHCO₃ / CH₂Cl₂ / 1.5 h / 45 °C

8.1: KH / tetrahydrofuran / 1 h / 0 °C

9.1: 176 mg / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 20 h / 20 °C

10.1: 95 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

11.1: 95 percent / Bu₃P / dimethylformamide / 4 h / 20 °C

With Grubbs catalyst first generation; oxalyl dichloride; trimethylsilyl iodide; tributylphosphine; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.1: Grignard reaction / 5.1: Swern oxidation / 6.2: Wittig reaction;

DOI:10.1021/jo0603025

upstream raw materials:

(R)-3-[(2S,3R,4aS,8aS,9aR,10aR)-3-(tert-Butyl-dimethyl-silanyloxy)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-2-yl]-2-methyl-propan-1-ol

diphenyldisulfane

(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

(2S,3R,4aS,8aS,9aR,10aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracene

Downstream raw materials:

C₄₇H₆₂O₉

9-[7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-4,5a,10-trimethyl-8-vinyl-4a,5a,6,6a,8,9,10,11,11a,12a,13,13a-dodecahydro-2H-1,5,7,12-tetraoxa-cyclohepta[b]anthracene

2-{3-[7-benzyloxy-6-(2-benzyloxy-ethyl)-2,6,8a-trimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-2-methyl-3-phenylsulfanyl-propyl}-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-ol

C₅₈H₈₂O₉SSi

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